Jeff Reifman has written an interesting article "Microsoft's Sacred Cash Cow" about Microsoft's past, present, and possible future.
I use Microsoft OS (XP pro) & Office software at home & work. Maybe I've been luckly as since moving to Windows XP I've had few hassles installing, updating, or using windows software.
Windows 9x was not so pain free...
As the CAD software I use is Windows based (no option for me there) I haven't had much experience with the alternatives. Perhaps I don't know what I'm missing!